1-Aminohydantoin → 1-[(E)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidine-2,4-dione

HRID 456099

反応式

HRID 456099 の反応式
[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9]([C:12](=O)[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.[NH2:26][N:27]1[CH2:31][C:30](=[O:32])[NH:29][C:28]1=[O:33]>CO>[F:1][C:2]([F:25])([C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:3]1[N:7]2[N:8]=[C:9](/[C:12](=[N:26]/[N:27]3[CH2:31][C:30](=[O:32])[NH:29][C:28]3=[O:33])/[CH3:13])[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1

参加物

4

反応物 2

HCID 728231-AminohydantoinHCID 581904681-(3-(Difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone

生成物 1

HCID 716998961-[(E)-1-[3-[difluoro(quinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]ethylideneamino]imidazolidine-2,4-dione収率 23.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A solution of 1-(3-(difluoro(quinolin-6-yl)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)ethanone (20 mg, 0.059 mmol) and 1-aminoimidazolidine-2,4-dione (13.6 mg, 0.12 mmol) was stirred in MeOH at room temperature over a weekend. Light yellow solid was filtered to give the title compound (6 mg, 0.014 mmol). The filtrate was purified on HPLC (acidic with 0.05% TFA) to give the title compound as TFA salt (8 mg, 0.0145 mmol). The combined yield was 48%. 1H-NMR (400 MHz, DMSO-d6) δ ppm 11.46 (s, 1H), 9.02 (d, 1H), 8.55 (d, 1H), 8.48 (s, 1H), 8.46 (s, 1H), 8.18 (d, 1H), 8.0 (s, 1H), 7.98 (s, 1H), 7.65 (d, 1H), 4.54 (s, 2H), 2.24 (s, 3H). LCMS (method B): [MH]+=437.1, tR=2.06 min.

後処理

  1. filtrationLight yellow solid was filtered

出典と根拠

ORDレコード
ord-8d7755e77f56488fbbc965803727bbac
出典データセット
uspto-grants-2013_07
特許番号
US08497368B2

関連ノート

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